| Stevie Franczek (Sr.) | 2019 IHSAA New Prairie Sectional Boys Cross Country Meet | 2019 IHSAA New Prairie Sectional Boys Cross Country Meet | 4 | 00:16.40 |
| Stevie Franczek (Sr.) | Wheeler Invitational Boys Cross Country Meet | Wheeler Bearcat Invite | 1 | 00:16.58 |
| Hudson Hall (Sr.) | 2019 IHSAA New Prairie Sectional Boys Cross Country Meet | 2019 IHSAA New Prairie Sectional Boys Cross Country Meet | 21 | 00:17.10 |
| Steven Jarvis (So.) | 2019 IHSAA New Prairie Sectional Boys Cross Country Meet | 2019 IHSAA New Prairie Sectional Boys Cross Country Meet | 25 | 00:17.33 |
| Zach Jarvis (So.) | 2019 IHSAA New Prairie Sectional Boys Cross Country Meet | 2019 IHSAA New Prairie Sectional Boys Cross Country Meet | 36 | 00:18.01 |
| Steven Jarvis (So.) | Wheeler Invitational Boys Cross Country Meet | Wheeler Bearcat Invite | 9 | 00:18.19 |
| Bobby Emery (Sr.) | 2019 IHSAA New Prairie Sectional Boys Cross Country Meet | 2019 IHSAA New Prairie Sectional Boys Cross Country Meet | 44 | 00:18.41 |
| Zach Jarvis (So.) | Wheeler Invitational Boys Cross Country Meet | Wheeler Bearcat Invite | 13 | 00:18.46 |
| Liam Hostetler (Sr.) | Wheeler Invitational Boys Cross Country Meet | Wheeler Bearcat Invite | 14 | 00:18.51 |
| Liam Hostetler (Sr.) | 2019 IHSAA New Prairie Sectional Boys Cross Country Meet | 2019 IHSAA New Prairie Sectional Boys Cross Country Meet | 53 | 00:19.06 |
| Evan Nowak (Sr.) | 2019 IHSAA New Prairie Sectional Boys Cross Country Meet | 2019 IHSAA New Prairie Sectional Boys Cross Country Meet | 68 | 00:20.51 |
| Tyler Kimberlin (So.) | Wheeler Invitational Boys Cross Country Meet | Wheeler Bearcat Invite | 40 | 00:22.57 |
| Nick Slutsky (Sr.) | Wheeler Invitational Boys Cross Country Meet | Wheeler Bearcat Invite | 41 | 00:23.15 |
| Nolan Henslee (Fr.) | Wheeler Invitational Boys Cross Country Meet | Wheeler Bearcat Invite | 51 | 00:25.56 |
| Josh DeRolf (Fr.) | Wheeler Invitational Boys Cross Country Meet | Wheeler Bearcat Invite | 53 | 00:27.32 |
